Journal
ACS OMEGA
Volume 4, Issue 15, Pages 16689-16700Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsomega.9b02796
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Funding
- Department of Chemistry at Universidad de los Andes
- Vicerrectoria de Investigaciones at Universidad de los Andes
- Colombian Institute for Science and Research (COLCIENCIAS) [120465843502]
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A convenient access toward novel fluoroionophores based on 1-(2-pyridyl)-4-styrylpyrazoles (PSPs) substituted at position 3 with donor or acceptor aryl groups is reported. The synthesis proceeds in two steps: the first one via Wittig olefination of the appropriate 4-formylpyrazole and then Mizoroki-Heck coupling to yield the desired products in an overall yield of up to 69%. Photophysical properties of products (4-styryl) and their intermediates (4-vinyl) were explored, finding that they have strong blue-light emission with high quantum yields (up to 66%) due to ICT phenomena. The 3-phenyl PSP was studied as a turn-off fluorescent probe in metal ion sensing, finding a high selectivity to Hg2+ (LOD = 3.1 x 10(-7)M) in a process that could be reversed with ethylenediamine. The sensing mechanism and binding mode of the ligand to Hg2+ were established by HRMS analysis and H-1 NMR titration tests.
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